By Jake Pearson, ProPublica
The nonprofit news organization ProPublica provided the stake for writer Jake Pearson, then sent him off to explore the world of problem online gambling firsthand. This is Part II of Pearson’s three-part story, originally published in its entirety on September 26, 2026 in ProPublica. You can find Part I HERE.
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Three days after the Yankees game, on May 7, following yet even more parlay losses, DraftKings served me a “responsible gaming” pop-up video—the first I’d been served in the app since the New York-mandated one on April 25.
“Took a loss? Now take a beat,” it read, directing me on how to visit the “My Stat Sheet” page on the app, where I could set a budget or impose limits on my ability to spend. I clicked “Maybe Later,” and the interruption was over.
But DraftKings’ apparent concern for my well-being was belied by a promotion the company sent me just hours later: A 20 percent profit BOOST on bets of up to $250 for an unlimited number of live microbets on baseball plate appearances. This was exactly the kind of bet that had led me to lose so quickly at the ballpark. Now the company was encouraging me to run it back at even bigger dollar amounts for as many times as I wanted until the promotion expired later that day. “Bet, settle, repeat!” read the push notification that popped up on my phone. I could practically hear the crank of a slot machine lever.
When I described this bet-pause-promote progression to Lori Kalani, DraftKings’ responsible gaming chief, she told me she’d “take that back” to her team for review but added, “I just don’t think we should be drawing broad conclusions from, you know, your single account, what you did.”
A few days later, exactly two weeks after my first big night of loss chasing during the Knicks game, I was formally accepted into the VIP program and assigned my very own, personal concierge. It had taken only three weeks and $5,800 in deposits on the app. My rep said he’d be “keeping an eye out for opportunities and perks tailored specifically” to my account, plus “reminders about Responsible Gaming.”
I could text him directly. I could reach out for special treatment. Isaac Rose-Berman, a professional sports bettor and policy expert at the American institute for Boys and Men, explained to me that this meant I could ask for “bonus bets,” free one-time bets using house money, or, more commonly, “deposit matches,” extra house money called DK Dollars, that fattened up my account when I made a transfer from my bank. He said that sportsbooks are happy to provide these freebies to losers like me because they’ve assessed, rightly, that we’re likely to end up gambling it right back—and that the special treatment will keep us loyal. I’d be earning crowns that I could convert to DK Dollars as I climbed the tiers of the loyalty program, which I could use to bet more or buy merch. I couldn’t help but hope that I’d also get the really cool stuff. A personalized video from a major leaguer? Tickets to a game? Swag?
My rapid ascent to VIP at DraftKings made me wonder how its major competitor, FanDuel, would handle a problem gambler like me. So I repeated the behavior there, placing the same kinds of bets at the same odds over the course of a week on their app.
One night I blew $529 on playoff basketball bets and then chased my losses with a $750 wager on professional hockey, backing the Minnesota Wild in a high-scoring matchup against the Colorado Avalanche. When the Avs won and my money was gone, I found the only remaining live action I could: a cricket match between Indonesia and Malaysia.
Like most Americans, I have no idea what cricket is. But whatever. It was near midnight and this was work, so I deposited $500 and tried to put it all on Malaysia. That bet would’ve netted me $11,000 had Malaysia won, but FanDuel wouldn’t accept it and required me to lower my wager amount. When I later asked the company about this, FanDuel wouldn’t say whether it did so because it didn’t want to lose the money or out of a commitment to responsible gaming. In any event, I put $200 on Malaysia instead and, of course, lost.
The app also put some speed bumps in my way over the course of that night, prompting me with “Reality Check” reminders six times that showed me the amount of time I’d been on the app and the amount I’d wagered thus far.
And unlike on DraftKings, my weeklong betting behavior on FanDuel didn’t result in a VIP invite. When I reached out to FanDuel for comment, the company touted its responsible gaming tools. A company spokesperson added in a statement that FanDuel’s program is “designed to identify potential risk early and empower customers with real-time information about their play.” For some customers, the statement said, “trained specialists” will intervene “or apply protective measures, including limits or exclusion,” though the company didn’t say how often that happens and what it takes, exactly, to trigger those measures. The New York Times reported that FanDuel is one of several operators that have signed up with third-party firms that help gauge customers’ risk for problem gambling to curb it. DraftKings is not among them but said it has its own tools.
Over on DraftKings, things were heating up. A month into my experiment I’d already lost $4,671—enough scratch to buy a used car (with a lot of miles)—and my bet size was growing, too. I was getting used to risking large sums. I looked back on how nervous I’d been to place $200 bets when I first started and couldn’t believe that I’d been so naive.
I’d been wagering so much, in fact, that the quick-tap deposit buttons in the app had increased to $500, $750 and $950, making it even easier to mindlessly transfer large sums from my bank into my DraftKings account.
Computer scientists have a term for this choice of user design: They call it a “dark pattern.” Critics say this is a key way that apps essentially trick you into subscribing to or purchasing things you don’t want or need with just one click.
And boy, was I getting fed opportunities to click. I’d selected the open settings for notifications on DraftKings, and as a result I was just getting pummeled with push alerts to my phone. Sometimes there’d be six in a day, offering BOOSTS. In the app, they’ve even got their own tagline: “BOOSTS DON’T STOP.”
I was hoping for tickets to a game or swag or anything super cool, but so far my VIP rep had hooked me up with only a 12-month ESPN subscription. That and lots of promotions to bet, at all hours. On Saturday, May 16, as I was getting the kids home from my son’s baseball game, DraftKings pushed me an “Exclusive Offer” to double my winnings on any bet up to $250. I pieced together a parlay on the subway, placing the bet as my service cut in and out.
The Yankees were playing the Mets that night, and Rose-Berman had encouraged me to shoot the moon—to climb the tiers of VIP status—so I strung together a five-leg parlay for the full eligible amount. My payout, highlighted in purple at the bottom of my slip, would be $6,250 if it hit.
The Yankees lost, and I hit only one leg of my parlay. As I nursed my wounds I began to wonder: Would I have spent that $250 but for the promotion?
I promise you I wasn’t trying to lose. Sure, I was firing unlikely bets, but I wanted them to win. If you could lose intentionally then you could win intentionally, and gambling wouldn’t exist. Over time most gamblers lose, and like them my performance was trending southward consistently—and fast.
But then, heading into Memorial Day weekend, I got on a hot streak. In statistics, this is called variance, but colloquially we refer to it as luck. Over five days, I notched real wins betting serious cash. After winning $3,869 on parlays from a Yankees game and the thrilling double overtime Spurs win in Game 1 of the Western Conference finals against the Oklahoma City Thunder, I almost forgot that, net, I was still down $8,836. And you know what? I felt like Superman.
To my betting brain, I was flying high. I was hot. I contacted one of my advisers, Rob Minnick, himself a recovering gambling addict who hosts a YouTube channel about problem gambling, and asked what he did after big wins.
He told me to withdraw the deposit I’d made immediately before my hot streak and then bet the winnings left in my DraftKings account with gusto because, hey, it’s just house money.
“I always say on my channel, like all wins are just future losses because when you don’t stop, it eventually gets given back,” he said.
Today, nearly a quarter of all Americans, and half of men ages 18 to 49, say they have an active sportsbook account, according to the Siena Research Institute. And with the advent of prediction markets, millions more are believed to be betting on sports.
But companies like DraftKings and FanDuel don’t just offer sports action: You can also gamble on casino games like blackjack and roulette in the handful of states where that’s legal. The companies call it iGaming, and they want it to be legal everywhere that sports betting is.
“I do think it’s a when, not if, that a lot of these states are going to legalize iGaming,” DraftKings CEO Jason Robins said at a June investor conference. “Customers want it. The tax revenue potential is real. And so we’re seeing a lot of momentum develop in different states.”
New York doesn’t permit that kind of gambling, but New Jersey is one of the roughly half dozen states that does. Since I was headed down the shore for Memorial Day weekend and my DraftKings account was flush from playoff basketball betting, it proved to be the perfect opportunity to try out iGaming.
I logged into my account from the beach on May 22 and was hit with a reminder of the app’s responsible gaming suite of tools, including the option to set a budget. I bypassed the prompt with the swipe of a finger, and there, on the main page, was a shortcut straight to the card table.
I explored the expansive casino offerings: I played roulette and tried out blackjack. The cards were dealt on a table that looked straight out of Vegas but for your phone. I didn’t have to think about how much to wager because DraftKings had already done that for me: With the click of a button I could bet as much as $1,000 per hand. And I was struck by how DraftKings cross-promoted iGaming to the sports bettor.
That included “baseball blackjack” and “basketball blackjack”—a regular deck of cards but instead of a felt card table background, there was a baseball diamond or basketball court.
I didn’t think much of that until after I bet on the Knicks and Cavs in Game 3 of the Eastern Conference finals the next day. At the bottom of the receipt of my bet slip, I noticed for the first time a “Suggested For You” section. Mine advertised baseball blackjack and basketball blackjack. The app was drawing me back to the table.
Not that I needed that hard of a nudge to start playing cards again.
Rose-Berman and I had discussed a strategy for the weekend: To escalate my compulsive betting late into the night, I transitioned from my usual sports fare to even faster, more exotic sports action (read: Czech table tennis) and then, ultimately, to the casino, following the path DraftKings was all but paving for me.
As I devolved in Jersey, Draft Kings promoted me to silver-tier status.
I’d played about 500 rounds of blackjack in a couple of days—accounting for just over half of my total betting activity during 10 weeks on DraftKings. By the end of the holiday weekend, I’d blown close to $3,000 on casino gambling. Before I left the Garden State, I asked my VIP rep whether there was any way to get just the casino stuff off my phone.
Days later he responded, informing me that, no, unfortunately, that wasn’t possible. But he did ask me whether I needed “help with setting in app limits.” I declined the offer.
DraftKings’ Kalani told me I wasn’t the first user to voice this complaint and said the company was working on allowing customers who’d rather just bet on sports to toggle off the casino on their phone.
I came away from my betting mania with an overarching takeaway: that the “responsible gaming” prompts that were served to me were no match for the product design pushing me to do more gambling.
While I was fighting off sleep to play cards, DraftKings occasionally threw me some responsible gaming speed bumps. Just before midnight, for example, a “time reminder” popped up on the blackjack table, telling me I’d been on the app for three hours and 45 minutes.
The pop-ups were barely disruptive: They covered a small part of the screen and could be swept away in a second. The design of the blackjack game, by contrast, facilitated betting big and chasing losses. That’s because DraftKings has made doubling your bet one of the options you’re served in between hands—literally enabling doubling down in a millisecond with the push of a thumb.
My adviser Rob Minnick, who, in addition to hosting a YouTube channel on problem gambling has co-founded a nonprofit industry watchdog that Rose-Berman advises, told me this dynamic pretty much summed up how he has come to understand the industry’s “responsible gaming” approach.
“It’s like an entire system that’s just built to appear to be doing something good while giving them basically like a free pass to do everything bad by saying, ‘Hey, we told you, you know, you have a responsibility, it’s your fault,’” Minnick said.
In a statement, DraftKings disputed that characterization, saying that all 5,000-plus of its employees are trained on responsible gaming every year and that it’s “not a side initiative. It is embedded across our business and essential to DraftKings’ long-term sustainability.”
But either way, Minnick and others said the framework for protecting consumers shouldn’t be entrusted to a publicly traded company that’s driven to grow revenue. “It’s unfair for us to expect or require a private business to do something that goes against its own mission of generating profit, right?” Minnick said. “Well, if you choose the industry standard, it’s going to be the least effective means.”
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Part III of this story will be posted in The Advance on Thursday..
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